Process for the conversion of unsaturated fatty acids, their glycerids and other esters into the corresponding saturated compounds.



F. BEDFORD & G. E. WILLIAMS. PROCESS FOR THE CONVERSION OF UNSATURATED FATTY ACIDS, THEIR GLYOERIDS, AND

OTHER BSTERS INTO THE CORRESPONDING SATURA' IED COMPOUNDS.

APILIOATION FILED AUG.14,1911.

1,026,339. Patented May 14, 1912.

fir/67112715 74426 a UNIT D STATES PATENT OFFICE.

FRED BEDFORD AND CHARLES EDWARD WILLIAMS, SLEAFORD, ENGLAND.

PROCESS FOR THE CONVERSION OF UNSATURATED FATTY ACIDS, THEIR GLYCEBIDS, ANDiOTHER ESTERS INTO THE CORRESPONDING SATURATED COMPOUNDS.

' Specification of Letters Patent.

Patented May 14, 1912.

Application filed August 14, 1911. Serial No. 844,020.

.7 '0 all whom it may concern Be 1t known that we, Faro Bum-01m. Ph. 1)., 13. Se. Loud. and CHARLES Enwann humans, subjects of the King of Great the conversion of unsaturated fatty by Ipat-iew Britain and Ireland. and residing at. Sleaford, in the county of Lincoln, England, have invented certain new and useful improvements in or relating to processes for acids, their glycerids and other esters. into the corresponding saturated compounds.

This invention relates to a process for the conversion of unsaturated fatty acids, their glycerids and other esters into the corresponding saturated compounds. and has for its object to simplify and cheapen the carrying out of such processes.

It has hitherto been proposed to cll'ect the conversion of unsaturated compounds as set outabove into the corresponding saturated compounds by treatment with hydrogen in the presence of eatalvzer, the latter being "always applied in the form of metal in a finely divided state. Finely divided copper oxid has also been proposed in'conncetion with the conversion of liquid oleic acid into thesolid in accordance with experiments (Eerie/d0 rler Deufsch. 12cm. Gas. 40. 1281-1907. and 42. 2091-1909) who was also able to hydrogenate certain organic combinations. viz., benzol. naphthalene and some other aromatic hydrocarbons as well as phenal naphthol, benzophenenc and acetone in the presence of nickel oxid, but in this case it was necessary to apply the hydrogen under very great pressure-about 100 atmospheres. The processes set out above. however, were necessarily expensive and uncertain on account of the ditlicult and extensivetechnical operations required for their proper carrying out. We have found. however. that the application of metallic oxids as catalytic agents in the conversion of unsaturated fats or fatty acids leads to a cheap and highly successful process, capable of being carried out at pressures commonly met withinautoclave processes such sary to force as are carried out in soap works and-even at atmospheric pressure and in which it is not necessary to apply the hydrogen under pressure greater than that which is necesit through the substance to be treated.

The accompanying drawing illustrates a simple and convenient form of apparatus that may be employed for the presentprocess.

In carrying our invention into eli'ect we employ the catalyzer in the form of' an oxid. nickel oxid being found to be the most rapid of all the catalytic oxids in its action, only one-halfto one per cent. of nickel oxid being in general required to be added to the oil, the latter being placed in any convenient form of tank or vessel a .which'mav be heated by superheated steam passing through the coil 6 or by a fire, oil-bath or other suitable means, and through which hydrogen may be forced fr'om the spray, or ring pipe 0.

Itis to be understood that the hydrogen or commercial gas containing hydrogen employed for the reduction is to be previously freed from injurious substances, for example, according to the method described in British specification No. 3752/10, while the organic substance to be reduced is also purified by distillation or otherwise.

The following'arc given by way of example only of results obtainable by the use of our invention, viz.:

Example 1: liters of purified linseed oil are heated to a temperature of about 255 C., and 0.5 kgs. of fine nickel oxid or latter is after 4.1- hours 355; after 5. hours 42 and it may be easily increased to 47 or over. The nickel oxid or protoxid is not reduced during this process to metallic nickel and it is only when an unnecessarily large excess of the catalytically acting metallic oxid is added that it contains a certain percentage of metal after completion of the process.

A parallel experiment, in which other conditions being the same, the like or even double the quantity by weight of freshly reduced metallic nickel is used, shows that after 5% hours at ordinary temperature linseed oil does not solidify at all. Instead of nickel oxid in Example 1 twice the quantity of cobalt oxid may be employed.

Sova oil and cotton oil when treated in an similar manner to that set out. in Example 1 give similar results.

We have found that during the process, provided pure hydrogen is used, only a small amount of .hydroxylated fatty sulr stance is formed.

A Example 2: 50 liters of purified oleic acid are heated to a temperature of about 255 (1, and 1% of finely divided nickel oxid or protoxid is added, a powerful stream of commercial electrolytic hydrogen, which V invariably contains oxygen in "arying provarying the quantity of the-metallic oxid, but we prefer to employ varying proper portions, being forced through the heated oleic acid. In this case, in addition to stearic acid, varying quantities of hydroxystearic acids are formed, depending .upon

the amount of oxygen present, the chief of such acids being the mono-hydroxystearie acid. v 1 Similar results may be brought about by i tions .of air or oxygen present in the hydrogen rather than to unduly increase the amount of metallic oxid although we have found that there is a limit to the amount-of oxygen which is to .be present forefiicient working of the process.

Example 3: Purified fish oil is heated with one per cent of nickel oxid to 255 and 'a current of hydrogen, previously freed from injurious substances, is passed through. After a few hours the fish oil possesses a solidifying oi'nt of'over 30 C. which may beeasily ra sed to 40 C. and over. v-

Example 4': Purified linseed oil, treated with copper or iron oxid gives stearin,'but

the recess is much slower than when nickel oxi is employed. t

Having now particularly described our invention whatwe claim as "new and desire to secure by Letters Patent is 1. A process for the conversion of unsaturated fatty acids, their glyeerids and other esters into the corresponding saturated stances to be reduced with purified hydrogen in the presence of heated finely dividedfinely divided metallic oxid.

.4. A process for the production of hydroxy-fatty acids which consists in treat.- ing unsaturated fatty acids, their glycerids and other esters with purified hydrogen mixed with oxygen, the amount of the latter gas being varied as desired to suit the requiredamount of hydroxylated fattysubstances.

In testimony whereof, we affix our signatures in presence of. two witnesses.

FRED BEDFORD. CHARLES EDWARD WILLIAMS. Witnesses:

Jno. WM. BELL, v HAROLDQD. THACKER.

compounds which consists in treating sub- 

